Breaking the Inertia: Midlife Reinvention

Midlife reinvention rarely begins with inspiration. It usually begins with an uncomfortable amount of effort that nobody else fully understands yet.

The Beginning Often Looks Unimpressive

At 56 years old I’m preparing to hike to the bottom of the Grand Canyon one more time before my left knee is total shit.

But you don’t train to hike the Grand Canyon by hiking in the Grand Canyon.

Before I hit the canyon trails, there needs to be a period of preparation. Yes, that means preparing my body for the physical assault I plan to perpetrate on it. But also, I need to study and prepare for the specific challenges, both physically and mentally, I will face.

This includes:

• Which trail to hike – the Bright Angel Trail is a very different experience than the South Kaibab Trail

• What time of year – temperature is a big factor on stamina, especially in the afternoon

• Day hike or camping – hiking down to the Colorado and back up in a single day (as opposed to reserving overnight camping inside the canyon) exposes you to the most heat when you are at your most fatigued on ascent

• Water availability – some trails have water stations, others do not – that means packing extra water, and water is heavy

You get it. These aren’t secret ingredients. It’s not mind-blowing that preparation and training are essential to achieving a preferred outcome. This is not a piece about hiking, either.

It’s about midlife reinvention, and how we approach entering Midlife-Plus by starting our own solo business.

At midlife we are wiser than we’ve ever been, and getting wiser with every passing year. (I assert that if we’re actively engaging with aging our wisdom grows exponentially.) We know preparation is necessary, but the real key is how we conceptualize and approach this new phase of our lives.

People often imagine transformation as one dramatic act:

• quitting the job

• launching the business

• hiking the canyon

But the real battle is usually much less cinematic. It’s the phase where you are still fundamentally the same person…

…but you begin acting against the inertia of your old life.

Surely you’re familiar with the Western interpretation of Lao Tzu’s proverb from the foundational Taoist text, the Tao Te Ching:

The journey of a thousand miles begins with a single step.

In Western culture, the phrase is heavily used as a motivational slogan to overcome procrastination and tackle intimidating, long-term goals.

But I’m thinking about it here as a means to just get moving, and the path will become clear as you accumulate steps. In the early stage of transformation, movement matters more than motivation.

(A purer translation is that the long journey “begins beneath your feet,” which is about being present in the moment and mindful of the immensity of the task you are preparing to undertake – this works here as well)

You learn along the way what works and what doesn’t. And you do more of what works and remove what doesn’t. Lather, rinse, repeat. Simple as that. And along the way your motivation becomes clearer as well.

What started as:

“I want to start my own solo business to protect myself from being downsized”

may become:

“I am starting my own business because I want to evolve into something new in the one-and-only life I get.”

So here’s the thing many of us fail to consider at the outset: the early stages of transformation often look unimpressive from the outside.

Repetition. Fatigue. Tiny progress.

But that’s how inertia breaks.

Breaking Inertia

I worked a grueling job collecting garbage door-to-door at apartment complexes at night. 5 hours up 3 flights and back down, carrying a bag as tall as me, filled with 60 pounds of other people’s garbage.

Not because it was satisfying.

Not because it was inspiring.

I did it because movement mattered more than inspiration.

Motivation doesn’t happen because of some “inspiring” quote painted in cursive on a piece of distressed faux driftwood from some hobby shop. It happens because you take action and start moving.

We can end up waiting indefinitely to be motivated by the right message of inspiration. All this amounts to is procrastination. And this flavor of procrastination is a result of a fear of failing.

So why garbage? There are plenty of ways to jump-start a canyon-hiking prep regimen, like going to Austin High and running bleachers. But there was something appealing to my blue-collar romanticism in this gritty training montage. And you don’t get paid to run bleachers.

Every time I dragged my ass up from a nap to go to this job (this was a second job in addition to my full-time, btw), I groaned and bitched and moaned. Still, I had made a commitment to Valet Living and I was expected to show up.

From the outside, it probably looked irrational: physically exhausting, unglamorous, unsustainable.

Internally, it was something much more important: proof that I was willing to begin.

But once I start my evening, on the first 3-story flight of the night, I feel the power of iteration accumulating towards my goal, and I imagine the hike that will get me to the canyon’s inner rim, the mighty Colorado thundering half a mile below, to watch the magnificent sun set into the western end of the gorge, slowly chased to the horizon by a darkening purple sky.

We underestimate lifestyle and social inertia because it’s invisible, and by midlife, this inertia is powerful. Your routines have calcified and your identity is hardened, carved by decades of responsibility. As your obligations multiply, you realize how finite your energy is.

This is the moment it becomes more imperative than ever to shake yourself loose and start thinking about the next phase of your life. How will you choose to take control of it?

The first breakthrough isn’t inspiration. It’s motion.

The first victory isn’t success. It’s disrupting the pattern.

You Build Capacity Before You Need It

(get ready for some lists so we can get through a lot real fast!)

Nobody wakes up ready to hike the Grand Canyon at 56. You build the capacity slowly, long before the descent begins.

And the same thing happens in business.

Before:

• confidence

• income

• momentum

• identity change

There’s usually a quieter stage:

• awkward effort

• inconsistent progress

• fatigue

• uncertainty

• repetition

The early phase is less about results than adaptation. You’re teaching yourself “I am still capable of becoming someone new.”

That’s the real transformation.

And I get it. We’re exhausted at times, and relaxation and recharge are requirements of a sane life. Most “start a business” advice accidentally creates more inertial resistance, keeping you stuck.

What you don’t need is more advice on:

• Branding

• Funnels

• Websites

• Niche selection

• Monetization models

• Content strategies

Don’t discount the importance of any of this. All of this is important and necessary to effectively build a successful solo business. But don’t put the cart before the horse.

What you do need first is to:

• Rebuild adaptability

• Reconnect with curiosity

• Develop self-trust

• Accumulate small proofs of capability

Even though we need to develop a mindset of becoming entrepreneurs, we don’t need all the added pressure of “becoming entrepreneurs,” at least not at the beginning of the process. What we need are small acts of capability-building that quietly reawaken our agency.

I mentioned above that we need to reconnect with our curiosity. But...how?

Try performing a quick “Curiosity Audit” and get some quick insight into what gets you excited. Ask yourself some questions like the ones below, and jot down some thoughts.

• What subjects make you lose track of time? (doom-scrolling doesn’t count!)

• What problems do you naturally research?

• What conversations energize you instead of drain you?

• What did you abandon because it seemed impractical?

So often our curiosity gets suppressed by seemingly endless obligations. But when it comes to discovering what you want to base a solo entrepreneurial venture on, curiosity is frequently the trailhead (see what I did there?) to meaningful work.

The Psychological Shift We’re Really Talking About

Just like you don’t train for hiking the canyon in the canyon, you don’t start a solo business by quitting your job.

• Commitment to a new thing is not a dramatic, performative gesture

• You build capability to be prepared for crisis. - so you certainly don’t want to create crisis before you build capability

There’s an old motivational phrase about taking time off work that is some variation of:

“When you get to the end of your life, are you going to be glad you didn’t take off work that day to go to that [special thing]?”

So when it comes to building your escape hatch out of a job you can’t stand, are you going to look back and be glad you didn’t explore starting something new? Are you going to be happy you decided to grind away to 80?

Inertia-Breaking Action Steps

These are the steps I took initially to prioritize movement over inspiration. You don’t need a clear path to an end goal. You only need to start moving, consistently repeat the movements, and clarity will emerge gradually.

• Write 50 words a day – EVERY day

  • What does your ideal life at 70 look like?

  • What are you wanting ‘tomorrow’ that you don’t have ‘today’?

• Read a book!! (I recommend reading Simon Sinek at least twice during your transformative phase; it hits different each time)

  • Start With Why – Simon Sinek

  • Be Useful – Arnold Schwarzenegger

To your continued growth.